The compound 1-(4-((1R,2S,3R)-1,2,3,4-tetrahydroxybutyl)-1H-imidazol-2-yl)ethanone (THI) is a minor constituent of Carmel Color III, and reportedly lowers circulating lymphocyte counts in rats. Methods of preparing THI have been reported. See, e.g., Kröplien, U. and Rosdorfer, J., J. Org. Chem. 50:1131-1133 (1985); U.S. Pat. No. 4,567,194 to Kröplien et al.; Cliff, M. D. and Pyne, S. G., Tet. Lett. 36(33):5969-5972 (1995); Cliff, M. D. and Pyne, S. G., J. Org. Chem. 62:1023-1032 (1997). A particular method reportedly provides THI in an overall yield of 46%. See Halweg, K. M. and Büchi, G., J. Org. Chem. 50:1134-1136, 1135 (1985).
It was recently reported that certain imidazole-based compounds are potent inhibitors of immune response, and may be useful in the treatment of diseases such as rheumatoid arthritis and type I diabetes. See U.S. patent application Ser. No. 11/698,253 to Augeri et al., filed Jan. 25, 2007. In order to facilitate their testing and use, additional methods of their synthesis are desired.